Carbon tetrabromide → Methyl 4'-(2-bromoethoxy)-3-(isopropylthio)-4-biphenylcarboxylate

HRID 2220402Notes

Reaction equation

HRID 2220402 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[C:13]([S:21][CH:22]([CH3:24])[CH3:23])[CH:12]=2)=[CH:7][CH:6]=1.[Br:25]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:25][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[C:13]([S:21][CH:22]([CH3:24])[CH3:23])[CH:12]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69102146Methyl 4'-(2-hydroxyethoxy)-3-(isopropylthio)-4-biphenylcarboxylate

Product 1

HCID 69103348Methyl 4'-(2-bromoethoxy)-3-(isopropylthio)-4-biphenylcarboxylateYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4′-(2-hydroxyethoxy)-3-(isopropylthio)-4-biphenylcarboxylate (124 mg) and tetrabromomethane (285 mg) in tetrahydrofuran (1.86 ml) was added triphenylphosphine (207 mg) and stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo, and the residue was purified with silica gel column chromatography to give methyl 4′-(2-bromoethoxy)-3-(isopropylthio)-4-biphenylcarboxylate (142 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-523a535b547247b7bd71b4ada36b7b3d
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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